Methanesulfonyl chloride → 1-(Diphenylmethyl)azetidin-3-yl methanesulfonate

HRID 2258587Notes

Reaction equation

HRID 2258587 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][S:20]([CH3:19])(=[O:22])=[O:21])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-benzhydryl-azetidin-3-ol (50 g, 0.208 mol) in dry pyridine (500 mL) was cooled to 5° C. Methane sulfonyl chloride (16.2 mL, 0.208 mol) was added over 30 minutes. The mixture was slowly (12 hours) brought to ambient temperature and stirring was continued for additional 2 hours. The solvent was removed in vacuo at 40° to 50° C. The residue was redissolved in methylene chloride, washed with water (2×), and dried. The crude material was triturated with a solution of t-butylmethylether/petroleum ether (15:85), to produce the purified product as crystals. (53 g, 80% yield). M.Pt.: 85°-87° C. MS

Workup

  1. custom(12 hours)
  2. custombrought to ambient temperature
  3. customThe solvent was removed in vacuo at 40° to 50° C
  4. dissolutionThe residue was redissolved in methylene chloride
  5. washwashed with water (2×)
  6. customdried
  7. customThe crude material was triturated with a solution of t-butylmethylether/petroleum ether (15:85)

Sources & evidence

ORD record
ord-6b81c2f3dfb249dda239cbab86067447
Source dataset
uspto-grants-1997_08
Patent number
US05661173

Reaction notes

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